Best Adrian Monk/Natalie Teeger Moments from Season 5 — 5×05 & 5×06

Note: As a diehard Monk/Natalie shipper, I’ve decided to relive the series by highlighting some of the best moments between the two characters. I think Season 5 was a turning point for Monk and Natalie. It seems that the writers finally settled on the kind of character they wanted Natalie to be (note the significant wardrobe change from this point on), which allowed the on-screen M/N chemistry to develop into its familiar season 5-8 form.

Natalie’s affectionate side with Monk was on display most of the time in Season 5, resulting in quite a lot of contact (not shippy, but definitely friendly/tender/supportive) in many episodes. Still the season was a bit uneven because Traylor Howard was pregnant IRL and wasn’t in a ton of scenes from about the halfway point on. But there were still plenty of moments that were cute or funny or otherwise show how well Monk and Natalie know each other. I’m listing them chronologically because Mr. Monk wouldn’t want it any other way!

Episode 5×05 — “Mr. Monk, Private Eye”: This was not a very strong episode, IMO. M/N spent most of the time bickering (and not in a cute, couple-y way) and I just didn’t like how the whole PI thing was dropped after this without even a mention. Another aspect that bothered me was Linda Fusco’s willingness to pay Monk $3,000 to find out who hit her car when the repair bill was only $900. WTF?

(3:14) — This long opening scene after the teaser featured several funny comments (pictured above).

(9:55) — Monk’s prank phone call to Natalie from across the office, saying he was being held against his will. Who says Monk doesn’t have a sense of humor?

Episode 5×06 — “Mr. Monk and the Class Reunion”: This was a great episode for Monk/Natalie scenes. In fact, when I originally watched the series for the first time, it was this episode that really made me consider the possibilities of a Monk/Natalie match. Sure, I’ve been pointing out little moments between the two in practically every episode since “Red Herring”, but those were only considered in hindsight. After “Class Reunion”, I started seeing their relationship from a whole different perspective.

(5:45) — Natalie: “You were Captain Cool? Why?” Monk: “Why do you think?” Natalie: “I don’t know.” Monk: “Why do you think?” Natalie: “I don’t know.” HA! Monk’s “cool” pose here was great, as was Natalie’s teasing mockery of it before she left. I also liked the playful punches to the arm, which reminded me of when she did the same thing in the tag in “Jury Duty”.

(12:06) — Natalie (after hearing why he was called “Captain Cool” and deciding to stay) runs up to Monk and wordlessly takes his arm, prompting a rare and genuine “Thank you” from him. This is one of my favorite moments of the ENTIRE series (pictured below).

(13:24) — Monk: “I was always just the guy with Trudy, just like you’re the girl with me.” Well, that gratitude didn’t last long!

(13:52) — Natalie: “I’m his assistant,” followed by the “Oh, so you two aren’t…” exchange with Diane. Not exactly what shippers want to hear, but at least they’re being mistaken for a couple!

(19:14) — Monk: “Maybe later. I want to show Natalie the library.” (Because it’s where he met Trudy.) It’s interesting that Monk wanted to share that special place with Natalie.

(19:31) — I love how Natalie listens so intently to Monk’s story. She seems genuinely interested and likes seeing him happy.

(23:05) — Natalie, on why Trudy chose Adrian over some guy who went on to become super successful: “Oh, Mr. Monk, she knew exactly what she was doing.”

(29:33) — Natalie gives Monk several excited little pats on the back before playing football. He doesn’t even react, which is a nice contrast to how he flinched when Diane’s husband touched him.

(40:43) — Monk and Natalie walking across campus at night past the bench where Monk first told Trudy he loved her. Natalie takes Monk’s arm and they continue walking off together in silence.